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<h1><a href="https://archiveofourown.org/works/27348775">Too small? Too bad</a> by <a class='authorlink' href='https://archiveofourown.org/users/Jellycatty/pseuds/Jellycatty'>Jellycatty</a></h1>

<table class="full">

<tr><td><b>Series:</b></td><td>Kinktober 2020 [19]</td></tr>

<tr><td><b>Category:</b></td><td>Teen Wolf (TV)</td></tr>

<tr><td><b>Genre:</b></td><td>Anal Sex, BDSM Scene, Barebacking, Butt Plugs, Come Inflation, Cuckolding, Kinktober 2020, M/M, Oral Sex, Rough Sex, Tied-Up Stiles Stilinski</td></tr>

<tr><td><b>Language:</b></td><td>English</td></tr>

<tr><td><b>Status:</b></td><td>Completed</td></tr>

<tr><td><b>Published:</b></td><td>2020-11-02</td></tr>

<tr><td><b>Updated:</b></td><td>2020-11-02</td></tr>

<tr><td><b>Packaged:</b></td><td>2021-05-07 01:29:00</td></tr>

<tr><td><b>Rating:</b></td><td>Explicit</td></tr>

<tr><td><b>Warnings:</b></td><td>No Archive Warnings Apply</td></tr>

<tr><td><b>Chapters:</b></td><td>1</td></tr>

<tr><td><b>Words:</b></td><td>1,875</td></tr>

<tr><td><b>Publisher:</b></td><td>archiveofourown.org</td></tr>

<tr><td><b>Story URL:</b></td><td>https://archiveofourown.org/works/27348775</td></tr>

<tr><td><b>Author URL:</b></td><td>https://archiveofourown.org/users/Jellycatty/pseuds/Jellycatty</td></tr>

<tr><td><b>Summary:</b></td><td><div class="userstuff">
              <p>Day 19 </p>
<p>Cuckolding</p>
<p>Derek gets a pounding while Stiles is made to watch</p>
            </div></td></tr>

<tr><td><b>Relationships:</b></td><td>Derek Hale/Stiles Stilinski, Derek/others</td></tr>

<tr><td><b>Series:</b></td><td>Kinktober 2020 [19]</td></tr>

<tr><td><b>Series URL:</b></td><td>https://archiveofourown.org/series/1949698</td></tr>

<tr><td><b>Kudos:</b></td><td>78</td></tr>

</table>

<a name="section0001"><h2>Too small? Too bad</h2></a>
<div class="story"><div class="userstuff module">
    
    <p>Day 19: Cuckolding</p>
<p>Stiles was bound to a st. Andrews cross, towards the side of the dungeon. They had decided to use a public room for tonight as it would maximise how many people would see Stiles in his humiliating predicament.</p>
<p>There were already patrons milling about, chatting, getting drinks from the bar or lounging in chairs, waiting for the show to begin.</p>
<p>Stiles was glad that the room wasn't too cold because he was already flushing as people eyed his naked body, his small, pert nipples and his semi-erect cock. If there had been a chill to the air, Stiles's dick would have shrunk and his testicles would have been trying to hide in his body.</p>
<p>Movement out of the corner of his eye pulled Stiles's attention away from his thoughts. Derek had finally given the nod that he was ready to begin and a beautiful woman led out the first man. He was burly but not quite as muscular as Derek, with thick red hair pulled back into a low ponytail. He was topless and as he entered the room and eyed Derek, he began opening his leather trousers before pushing the love of Stiles's life to the floor.</p>
<p>Derek shuffled them around so that Stiles had a view of both of them and he could see Derek winking at him before swallowing the man's cock beautifully.</p>
<p>For the next five minutes, the man fucked Derek's face while the Were's husband was bound and forced to watch. Stiles wasn't big enough to reach down Derek's throat like that and the humiliation of knowing that Derek was getting his deepthroating kicks elsewhere burned through him making him both embarrassed and hard as a rock.</p>
<p>When Derek finally had his fill, he pulled off and stood up. He was a man who knew what he wanted and he wouldn't hesitate to get it.</p>
<p>"You're going to fuck me now. You can lube yourself but don't prep me. I like the burn of being speared on a nice big cock." Derek then picked up a nearby spanking bench and placed it in the centre of the room. Taking off his robe, he bent over to lie his chest flat on the padding.</p>
<p>The other man busied himself with putting on a condom and lube, while Derek finally addressed Stiles.</p>
<p>"How does it feel baby? To know that some stranger is going to slide into my ass while you're forced to watch. Is it awful to know that you will never get to do this? To feel the tight grip of my hole? Because your little dick would never give me enough pleasure. It can never get down my throat or stretch my ass wide or deep, so random people need to plug me up instead."</p>
<p>Stiles shuddered and humped his cock into the air, wishing he could have friction.</p>
<p>"Yes, it's embarrassing that I'm too small to satisfy you, that you have to punish me for my small dick by making me watch how a real man would fuck you. I'm only good as a hole for you to fuck. My ass, my mouth, my hands and my cock are all yours to fuck however you see fit, Der" Stiles panted out, feeling winded from the arousal.</p>
<p>"And don't you forget it. I love fingering open your tiny little cocklet, fucking it open with a bullet vibrator like a pussy but you'll never fill me. Never - OH… Fuck, yessss," Derek was cut off by the red head's cock sliding into him firmly but slowly. The drag was exquisite and the burning sensation made Derek's cock leak onto the padded leather below him.</p>
<p>Derek's attention left Stiles at this point and he spoke to the guy who was fucking him.</p>
<p>"Go as hard and as fast as you like. Pound my ass but try not to hit my prostate too much. I've got a lot of men to get through tonight and if I come too early, it'll be unbearable."</p>
<p>The man nodded and set a brutal pace, purposefully angling away from Derek's prostate. The Were was moaning with every thrust, loving the feeling of being filled and used. All too soon the other man stilled, spilling into the condom. After a couple of minutes. The man kissed the back of Derek's neck, pulled out and left the room. Condom still on his dick.</p>
<p>Derek got up and walked over to Stiles. Bending over and spreading his cheeks, showing his gaping pucker to his husband.</p>
<p>"You see how open I am? His cock felt so good in me, so thick and long with powerful thrusts. Isn't it good that I can find someone else to fuck me so well since my mate isn't up to the task?" Derek mocked while Stiles nodded, eyes tearing up even while his cock was drooling.</p>
<p>Derek stepped up close to him.</p>
<p>"Do you need to safeword?"</p>
<p>Stiles shook his head passionately and Derek smiled and swiped some of Stiles precome from his dick and pushed it into the human's mouth, forcing him to taste himself. Stiles moaned and dripped more but Derek was distracted by another man being brought in by the hostess.</p>
<p>This man was tall and slim and had the face of someone who was probably nerdy as hell but also had a mean streak a mile wide.</p>
<p>There were no pleasantries with this guy. He stripped off and walked towards Stiles and Derek. His absurdly long cock slapping against his thigh as he walked.</p>
<p>He spun Derek around to face Stiles and ordered him to place his hands on either side of Stiles's head and tilt his hips down and ass up.</p>
<p>This position meant that when the long cock was pushed against his hole, which sucked him straight in until the man was so deep in Derek's bowels that he'd never been reached there before, he groaned directly into Stiles's face and sobbed in a single breath at the overwhelming feeling.</p>
<p>"Oh god, Stiles, he's so deep. I can feel him, he's right up in my colon, bulging my lower abdomen. It hurts so good, Baby."<br/>
Derek's breath was stolen from his body as the man started thrusting inside him, stretching him deliciously.</p>
<p>The man didn't move overly fast but his hard, punching thrusts were glorious. Although the man was nowhere near his prostate, Derek thought it was possible he might actually come from the stimulation of previously untouched areas.</p>
<p>As the man eventually began to speed up the motions, Derek needed more. He pushed away from Stiles and manhandled the stranger onto his back on the floor before quickly straddling him and taking his length into his body even deeper than before. He was whimpering constantly now, riding the man's cock for all he was worth, using both the depth and some careful angling to constantly rub against his prostate until he threw his head back with a cry and came over the stranger's stomach while the man filled his ass with his seed.</p>
<p>Panting, Derek climbed off the man and spun around to show Stiles his hole again, now with globs of come seeping out and down his thighs.</p>
<p>"Isn't it pretty Stiles? I'm all painted up like I'm supposed to be, ready for another dick to come and fill up my greedy hole. I bet you want it don't you baby? I bet you want to press your little cock into my messy hole and rut into me until you burst."</p>
<p>"Yes, Der please, yes I want to fuck you so much, I swear I'll do anything... ANYTHING for you." Stiles begged. His cock and balls were taut and painful at this point.</p>
<p>Derek sneered at him.</p>
<p>"Of course I'm not going to let you put that little clit into my ass, I wouldn't even feel it, my love. Only real dicks go inside my pussy babe, you know that. I need to swallow up something big like that last guy. Did you see how riding him made me come so hard without a single touch to my cock? It felt so good, I felt like a whore coming like that and I loved it." </p>
<p>Derek ran his fingers up the underside of Stiles's cock making him twitch and thrust erratically.</p>
<p>"Not yet baby. I've still got more come to take, gotta get me nice and full so I'm brimming over with multiple loads before I'll let your little cock cry."</p>
<p>Another nod from Stiles and another man was being brought in.</p>
<p>The next half an hour went by the same way, with Derek taking different size and shape cocks. Some emptying their load into a condom, some into his ass and Derek would show Stiles his hole after every single one.</p>
<p>One benefit to being a werewolf was that his ass healed and unstretched within minutes of no longer being filled, meaning he was able to hold the come inside slightly easier and also, every cock felt like the first cock he'd taken that night. </p>
<p>By the last Man, a very short fellow with the longest, fattest dick Derek had ever seen, he was ready to come again and was bouncing on the portly fellow like he was a bucking bronco.</p>
<p>"See love? Even this guy can satisfy me in a way you can't. You might be tall with long limbs but it doesn't equate to a good dick does it? He's not even attractive and he fills my hole up better than any man tonight. Even his balls are big and juicy, primed for being suckled on." Derek panted, winking at the man below him who he'd already had confirmation from that it was ok to 'humiliate' him with words. It's why this particular man got shortlisted. (heh short)</p>
<p>Hearing Derek humiliate him, the man got close to orgasm and Derek smelled it coming. He quickly clicked the pendant necklace that he was wearing and then gripped his shaft, thrusting into it twice before the man he was fucking came into him too.</p>
<p>Derek finally lifted his head to watch Stiles writhing in his bonds, sobbing. The pendant was linked to the butt plug, Stiles had inside him which was now vibrating persistently on his prostate.</p>
<p>It took only for Derek to shuffle over on his knees to show Stiles his ass again and this time pushing out the multiple loads inside him for Stiles to cry out and come, jizz splattering onto the floor next to the puddle Derek was causing.</p>
<p>The Were quickly clicked the pendant again, stilling the plug in Stiles before undoing the Human's bonds and pulling him into a loving hug.</p>
<p>Derek picked Stiles up into a bridal carry a few minutes later and took him into a private room where he gave them both a quick rinse in the shower and then ran a bath for the pair of them so they could soak and Derek could massage his husband's sore muscles after being bound for over an hour.</p>
<p>They would talk through the scene after their bath, food, hydration and a nap and then Derek would fuck Stiles's brains out until there was no doubt in his mind that he was good enough for Derek.</p>
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